The problem with tranched VC investments

In venture capital, tranching refers to investments where portions of the money are released over time when certain pre-negotiated milestones are hit. Usually it will all be part of one Series of investment, so a company might raise, say, $5M in the Series A but actually only receive, say, half up front and half when they've hit certain milestones. Sometimes something similar to tranching is simulated, for example when a VC makes a seed investment and pre-negotiates the Series A valuation, along with milestones necessary to trigger it.

In theory, tranching gives the VC's a way to mitigate risk and the entrepreneur the comfort of not having to do a roadshow for the next round of financing. In practice, I've found tranching to be a really bad idea.

First of all, the entrepreneur should realize that the milestones written in the document are merely guidelines and ultimately the VC has complete control over whether to fund the follow on tranches. Imagine a scenario where the entrepreneur hits the milestones but for whatever reason the VC gets cold feet and doesn't want to fund the follow on tranche. What is the entrepreneur going to do - sue the VC? First of all they have vastly deeper pockets than you, so at best you will get tied up in court for a long time while your startup goes down the tubes. Not to mention that it would effectively blacklist you in the VC community. So just realize that contracts are the right to sue and nothing more. The only money you can depend on is the money sitting in your bank account.

Here are some other reasons both entrepreneurs and investors should dislike tranching:

1) Makes hiring more difficult: Hiring is super critical at an early stage. A very reasonable question prospective employees often (and should) ask is "How many months of cash do you have in the bank?" How do you respond if the money is tranched? In my first startup, our full round gave us 18 months of cash but the first trance only a few months. Should I have said what I had in the bank- just a few months - and scare the prospective hire? Or should I have tried to explain "Oh, we have 18 months, but there is this thing called tranching, blah blah blah, and I'm sure the VCs will pony up." Not very reassuring either way.

2) Distracts the entrepreneur: The entrepreneur is forced to spend time making sure she gets the follow-on tranches. In many cases, she even has to go present to the VC partnership multiple times (each time requiring lots of prep time). Also, savvy entrepreneurs will prepare multiple options in case the VC decides not to fund, so will spend time talking to other potential investors to keep them warm. So basically tranching adds 10-20% overhead for the founders that could otherwise be spent on the product, marketing etc.

3) Milestones change anyways: At the early stage you often realize that what milestones you originally thought were important actually were the wrong milestones. So you either have to renegotiate the milestones or the entrepreneur ends up targeting the wrong things just to get the money.

4) Hurts VC-entrepreneur relations. Specifically, it encourages the entrepreneur to "manage" the investors. One of the great things about properly financed early stage startups is that everyone involved has the same incentives - to help the company succeed. In good companies, the investors and entrepreneurs really do work as a team and share information completely and honestly. When the deal is tranched, the entrepreneurs has a strong incentive to control the information that goes to the investors and make things appear rosy. The VC in turn usually recognizes this and feels manipulated. I've been on both sides of this and have felt its insidious effect.

There are better ways for investors to mitigate risk - e.g. lower the valuation, smaller round size. But don't tranche.